WFTW Body: 

In Matthew 5:3 Jesus says, “blessed are the poor in spirit.” This word “blessed” can mean “happy” or like the Amplified Bible says, “someone to be envied.” If you want to envy somebody on earth, don’t envy the rich person, don't envy the famous person, and don't envy the good-looking person. Envy the one who's poor in spirit, because the kingdom of heaven belongs to him. People with many other qualities, such as charisma and wealth, can have things on this earth and possess a kingdom on earth, but the kingdom of heaven belongs to the poor in spirit. In the long run, this is the one who is really to be envied, because his wealth is going to last for all eternity. When we think of our lifetime on earth, even if it's 70 or 80 years, if you really believe that man is an eternal being (eternity is never-ending, millions of years are like one second in eternity), what would 70 years be? Nothing! In 2 Peter, it says a thousand years is like one day before the Lord and one day is like a thousand years! In the light of eternity, our entire life on earth is very short.

A wise person is one who really seeks to have a future in God's kingdom, and here we are told that the one who's going to have the maximum possessions in God's kingdom is the one who is poor in spirit. This is a phrase that is not understood by many Christians because they don't seek to understand these seemingly confusing statements of Scripture. They just read and move on. One thing that helps me is to think in terms of an illustration. I find that when I think in terms of pictures, I get a clearer understanding of the Scripture. In fact, Jesus Himself explained many doctrines in terms of pictures, such as salt and light, and through many parables.

We can compare “poor in spirit” with “poor in body,” because man is spirit and body, and we understand what it is to be poor in body. A tramp or a beggar is poor in body, which means he does not have what it takes to care for his bodily needs. A really poor beggar who's living on the streets might go from house to house begging for his needs, only to get just enough to survive for the day, and then he would have to come back to the same house to receive some more for the next day. So applying that picture to the phrase, “poor in spirit,” we see that Jesus means a person who is aware of his spiritual need every day. He is describing a person who is just like that beggar, who is aware of his physical need every day and goes to some generous man's house for help. And if the man asks him, “What about what I gave you yesterday?” he would say, “That was finished yesterday - the money you gave me yesterday was just enough for yesterday's need, and again I am in need. I am penniless, I'm in need.”

A person who is “poor in spirit” is one who comes to God in that way, saying, “Lord I'm a needy person.” He comes to God every single day aware of his spiritual need, and asks for help to meet his spiritual need, just like the beggar would ask for help to meet his physical needs.

In the book of Proverbs, there is a verse that speaks about this condition. Proverbs 8 is a chapter on wisdom, and Christ is pictured here as wisdom, saying, “I, wisdom…” (starting in verse 12). He goes on to say that it is through wisdom that the world was created. And it says in verse 24 that He was there before the fields were there and the earth and everything else - when He established the heavens (verse 27), He was there. So wisdom is what we need, and it says, “Blessed is the man who listens to me, who watches daily at my gates.” Think of that beggar now, waiting at God’s doorposts. Just like a beggar waiting for his daily gift of money, we are to come before God as spiritual paupers every day.

We won't come like that unless we are needy. Rich people don't go begging at other people's houses; they would be ashamed to do it. A beggar is not ashamed because he's needy. He doesn't have money for food or his daily necessities, and he's aware of that. It’s only the person who's aware of his spiritual need every day who will come before God every single day and say, “Lord I'm a needy person. Please give me wisdom for today.” And as it says in Proverbs 8:35, “He who finds me finds life.” 

This is what it means to be poor in spirit: to be aware of our spiritual need constantly. The one who is aware of his spiritual need constantly, and who keeps seeking for wisdom from God, will possess the entire kingdom of heaven. If you see the kingdom of heaven as the riches of God's kingdom, the Bible says inEphesians 1:3, that God has blessed us with every spiritual blessing in the heavenly places in Christ. Every single blessing of the Holy Spirit is ours in Christ in the heavenly places. We can think of all the spiritual blessings in the kingdom of heaven as a huge mansion with thousand rooms, and the master key that opens every door of that mansion is a poverty of spirit. Blessed is the one who is poor in spirit, because he can possess the entire kingdom of heaven - that is, every single room of the mansion. The treasures in every room will be his, if he holds fast to this master key.